


After School Special

by raincoatdrown



Category: Supernatural
Genre: Adam Milligan is Not Forgotten, Adam Milligan is a Winchester, Alternate Universe - High School, Awesome Charlie Bradbury, Baby Jack Kline, Castiel and Dean Winchester and Sam Winchester are Jack Kline's Parents, Castiel is Claire Novak's Parent, Castiel/Dean Winchester Mutual Pining, Charlie Bradbury & Dean Winchester Friendship, Charlie Bradbury & Sam Winchester Friendship, Dean Winchester is Good With Children, Enemies to Friends to Lovers, Fluff, Internalized Homophobia, John House's A+ Parenting, M/M, Mutual Pining, No Smut, Sam Winchester Ships Castiel/Dean Winchester, Slow Burn, minor gilmore girls references bc i do what i want - Freeform, sorry I'm asexual
Language: English
Status: In-Progress
Published: 2021-02-06
Updated: 2021-02-06
Packaged: 2021-03-15 05:28:13
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 12,566
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29184015
Author URL: https://archiveofourown.org/users/raincoatdrown/pseuds/raincoatdrown
Summary: Dean Winchester is tired.Tired of working full time. Tired of raising his brother when he’s still just a kid himself. And tired of cleaning up the messes of his absentee father.Dean knows that juggling it all for two more years until Sam graduates isn’t going to be easy, but with a group of dorky teenagers, a weekly DnD campaign, and Cas in his life, plus a fictional apocalypse to stop, maybe they’ll all manage to make it through afterall.
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Comments: 6
Kudos: 20





	1. Freaks and Geeks

Dean loved his little brother. He really did. But why did he have to schedule his nerd shit on Dean’s only day off?

Dean spent every day except for Friday’s at Winchester Auto Repair, and Sam knew that. So was it too much to ask that he didn’t invite half a dozen dorky teenagers over to their house on the one day Dean didn’t have to spend underneath the hood of a car?

Apparently.

Sam had been running his weekly DnD campaign on Fridays for the better part of two years now, and despite the truly astounding amount of complaining Dean had done, Sam had made no attempts to try and reschedule it. It was almost like Sam wanted him to play or something. Which was ridiculous, because as a rule, Dean did not care about wizards, or fairies, or roleplaying in funny accents, or the fuck ever else went into Dungeons and Dragons. So as the clock rolled around to 3:45 Dean braced himself. Any moment now Sam and Co. would be getting off the bus and stomping their way to his front door to ruin his night. Perfect.

He could hear them coming before Sam even slipped the key into the lock. He could hear Charlie’s snorting laugh, and Sam’s token _Analyzing Books Meant for Middle Schoolers Like They’re Freakin’ Dostoyevsky_ voice from half a block away.

“Dean,” Sam called into the living room, “We’re ho-ome.” He drew out home into two syllables.

Dean wandered out of the kitchen like he hadn’t been actively waiting for his little brother to show up for almost half an hour.

“Hey Sammy,” he said, but then he turned his gaze to the redhead standing behind his freakishly tall little brother. “Charlie,” He grinned and he shot her some finger guns.

“Dean,” She said, and she stepped forward and stuck out her hand like she was going in for a fist bump, but Charlie and Dean’s handshake was a little more complex than that. It was a thing of beauty years in the making, complicated enough that Sam had never been able to replicate it, mostly because it continued to gradually evolve and change, month in and month out.

Charlie had always been his favorite of Sam’s friends. Even when Sam had first brought her over to their house, when they were seven and Dean was nine, he’d still thought she was cool then. Or too cool to be friends with Sam at least. She was kind of like the little sister he’d never asked for. She talked non-stop, dressed the way she wanted, and didn’t care what anyone thought of her. She was the type of person who existed outside of anyone's expectations of her, and Dean, as much as he might hate to admit it, had always envied that.

Standing next to Charlie was Chuck, as quiet, and jittery, and just plain weird as ever.

“Where’s the rest of the gang?” Dean asked sardonically, “Tired of playing with dolls every Friday night?”

“They’re not dolls,” Chuck muttered, “They’re miniatures.”

Dean personally didn’t see any difference. And anyway, it didn’t change the fact that they were definitely a couple of regulars short.

“Kevin will be over in a few, he’s got cello practice until 4:00,” Sam said, “And Gabriel got a car for his birthday over the weekend so he’s probably out joyriding.”

Dean snorted, “That’s a funny way of saying ‘slaughtering innocent civilians.’”

“And then we’re only missing- ”

“Me?” Jo asked, peeking her head into the open front door.

Dean blinked in surprise, “What are you doing here Jo?” he asked, his mouth turning down in a little frown.

“Sam invited me. Said they’re starting a new campaign today so they can add new players. I’ve been wanting to try DnD for a while.”

Dean didn’t know what to make of that. Jo was his friend first and foremost, not Sammy’s. They had graduated together a year ago. He hung out with her at her mom’s bar most nights after he got off of work, and he’d never heard anything from her about wanting to play Dungeons and Dragons. Plus it didn’t sit right with him that Sam had invited Jo to hang out with him and his friends. It wasn’t like Dean ever texted Charlie and invited her to things without Sam.

“I never pegged you for a nerd Joanna Beth.”

She shrugged, “I don’t know Dean, it seems fun.”

“Yeah, well,” he grumbled, “Have fun casting spells or whatever the fuck.” and with that, he threw himself down onto the couch and switched on the TV.

Unfortunately, it was still switched to the CW where the marathon of _Dr. Sexy, M.D._ Dean had been watching earlier was still airing. Dean cringed internally and fumbled to change the channel hoping no one would notice. It changed to some obnoxious Japanese game show. He glanced back at Sam and his friends, and Sam and Charlie seemed to be wrapt in conversation, but Jo was raising an eyebrow at him, and Chuck was nodding appreciatively.

“It’s the cowboy boots right?” Chuck said, gesturing at the TV.

“Cowboy boots?” Jo asked, a thin smirk flickering across her face.

“Dr. Sexy wears cowboy boots. It’s what makes him so sexy.”

Jo choked on a laugh, and Dean scowled and turned away. He hated to think that he had anything in common with Chuck, even something as stupid as watching a dumb hospital drama in his free time. Chuck was right about the cowboy boots though.

Kevin had arrived a few minutes later, and once the group had noisily raided the kitchen cupboards for snacks, they had disappeared into the basement. Dean had done his best to zone out and watch TV like he’d planned, but not half an hour later, the doorbell had rung.

Dean was at the door already when he heard the rumbling of too many high schoolers thudding up their creaky basement staircase; and Charlie’s socked feet, which were patterned with blue and bronze Ravenclaw eagles, slid across the tiled landing to Dean’s side.

Dean shot Charlie a small side-eye as he opened the door. He had no idea why Charlie Bradbury would ever be that excited to see _Gabriel_. But there he was, standing as expected. Slouching, wearing sweatpants, his eyes flashing with that ever-present mixture of something between mischief and contempt. If Chuck hadn’t had the misfortune of existing, Gabriel could’ve won the _Least Favorite Friend of Sam’s_ slot easily.

But standing behind him was someone Dean had never seen before. He was taller than Gabriel, and maybe a little older, with messy dark brown hair and blue eyes.

They were piercing, those eyes, not because they were startlingly bright or anything. It was just the way they were narrowed so intensely, brow furrowed. He was looking right at Dean, but he wasn’t meeting Dean’s eye. It was like he was both looking right through him and examining him under a microscope at the same time.

It was… unsettling.

Gabriel let out a small cough, and Dean realized that he was still standing with the door halfway open, clutching the doorknob.

“You good Dean?” Sam asked, clapping him on the shoulder.

“Yeah,” Dean said, shaking his head and stepping out of the way so that Gabriel and the guy, whoever he was, could get inside.

“Cas!” Charlie said, giving the kid a quick hug, “You are going to love DnD. I swear to you.”

Sam, picking up on Dean’s confusion, made introductions quickly, “Dean, Jo. This is Gabriel’s cousin, Castiel Novak. Cas, this is my brother Dean, and Jo Harvelle, a family friend of ours.”

“Hello Dean,” Castiel said, then he turned and shot a nod at Jo in greeting. His voice was shockingly deep, and strangely devoid of inflection. Dean didn’t like it. He gave off such a weird vibe. Dean wasn’t sure he’d seen him blink yet. And what kind of name was Castiel anyway?

“Your parents super religious or something?”

Castiel paused and then responded, “Yes. Very much so.”

Gabriel snorted, “Religious, in a cult. Whatever you want to call it.”

“They’re not in a cult,” Cas muttered.

“They raised you to believe that dinosaurs are a hoax and that you’ll burst into flames if you ever kiss a dude.” Gabe said rolling his eyes, and patting his cousin patronizingly on the shoulder, “That’s cult shit, Cassie.”

Cas had gone tight-lipped, and it was pretty obvious that he didn’t like talking about his family, so Dean made an effort to change the subject.

“So, you’re a junior? Like Sammy?”

Castiel shook his head stiffly.

“He’s a senior,” Sam supplied, “We have AP Government together though.”

“And I have English with him,” Charlie said brightly.

Dean didn’t see how Cas could’ve been a senior. That made Cas just a year behind him in school, and their little town didn’t allow for very many strangers. Dean knew most of the current class of seniors.

“Are you new to the district?” Dean asked.

“He used to be homeschooled,” Gabriel said, and again, Cas looked uncomfortable, so as tempted as Dean was to ask, he let it drop.

Despite Dean’s initial impression of him, now that he was standing in the house, looking around, Dean saw that Cas really did fit in with the rest of Sam’s group of friends. He and Kevin were dressed almost identically in slacks and button-downs. Kevin at least was wearing a pair of sneakers, but Cas was wearing brown dress shoes. He looked like a fucking junior accountant. Of course he’d be just as big of a nerd as the rest of them. And maybe he was creepy with all of his staring and monotone, but you couldn’t exactly expect normalcy from anyone related to Gabriel.

“Well, now that everyone’s here, we can get started,” Chuck said, clutching a Moleskine notebook tightly to his chest.”

“To the basement!” Gabriel declared.

“Excelsior.” Charlie echoed.

Dean watched as they filed down the staircase, one after another until it was only him and Sam left on the landing.

“You should join the game Dean, it’ll be fun.”

“It’s not really my thing Sammy.” he shrugged.

“Oh come on Dean,” Sam sighed, exasperated, “You end up watching us play half of the time anyway. I know you know all of the rules.”

“I do not watch you guys play that often.”

“You did last week, and the week before that, and the week before that, and- ”

“Shut it, Sammy. I’ve got better shit to do. Alright?”

“Yeah, whatever,” Sam said, rolling his eyes. “Have fun watching Dr. Sexy,” he muttered under his breath as he headed down the stairs.

“What did you say?” Dean called down after him.

“Nothing.”

“That’s what I thought.”

***

Dean did not watch them play that often. It was just that he always ordered food for them when it got close to dinner time, and once he was downstairs, sometimes there was cool shit going on.

Last session Gabriel’s character had been taking on a trickster God in a battle royale, and because Sam, the DM, had let Gabriel pick his weapon of choice, it had ended up a battle of insults. Which, perhaps unsurprisingly, Gabriel’s character had won.

Still, Dean did not go to watch them play. He also, pointedly, did not watch Dr. Sexy. Instead, he’d read for a while. Then he’d almost texted Benny before changing his mind. Then he’d almost texted his dad before changing his mind.

And then it had been time to go ask the dorks what they wanted for dinner.

As soon as Dean entered the basement he regretted not coming down sooner. It was Chaos.

“This is bullshit!” Gabriel was yelling, and he swept one of Chuck’s miniatures off of the card table with his arm for dramatic effect. “I want to be a gnome!”

“There are no gnomes in the Wild West!” Chuck said, looking more disheveled and twitchy than usual.

“I. Want. To. Be. A. Gnome.”

“Just let him be a gnome so we can play,” Sam said, burying his face in his arms.

“No. I wrote this campaign, humans and homebrew races only.” Chuck said firmly.

“Fine then. I’ve got a homebrew race for you.” Gabriel said through gritted teeth, “It’s like a human, but short, and with the exact stats of a gnome.”

Chuck set his jaw, and hissed out a disgusted, “Fine.”

“Is this a bad time to mention that I want to be a tiefling?” Charlie asked, “And Cas wants to be an aasimar.”

“It’s fine.” Cas said softly, “I can be a human.”

“No,” Charlie said, “It’s your first campaign, you should be whatever you want.”

“Why’d you guys even ask me to be the DM if you aren’t going to listen to me?”

Sam snorted, “Like you guys ever listened to me last campaign.”

"And we didn't ask you," Gabriel added, "You practically begged."

“It’s a Western?” Dean interrupted. Everyone at the crowded fold-out card table turned their heads to look at him.

Chuck looked relieved that someone seemed interested in his vision, “It’s supposed to be like, cowboys save the world from a demonic apocalypse. But apparently, nobody cares!” Chuck sucked in an incensed huff of air.

“That sounds pretty cool actually,” Dean admitted half-heartedly. He wasn’t one for elves running around with swords and magic wands, and those were the sorts of campaigns Sam always ran. But demon-hunting cowboys with guns. _That_ he could get behind. “Are there guns?”

“Yeah, there are guns,” Chuck replied, looking defeated.

Dean couldn’t believe the next words out of his mouth. “Can I play?”

***

Sam grinned and scooted down so that his brother could squeeze in another chair. There was a simple reality at work here that Sam had been aware of for years: Dean Winchester liked DnD.

He pretended he didn’t. He also pretended that he hadn’t read Harry Potter, even though Sam’s set of books had mysteriously disappeared for weeks at a time, one by one, and returned to his shelf all on their own. He'd admitted to liking Star Wars and Marvel movies after Charlie and Sam had practically force-fed them to him during their summer movie marathons, but only because one franchise had laser guns and “War” right in the title, and the other had punchy men in mech-suits. And even though Dean liked the MCU, you’d probably have to put a gun to his head to get him to pick up a comic.

Dean had always been so determined to limit his interests to things their dad would approve of if he found out about them. He acted like anything that wasn’t classic rock, or fixing cars, or playing first-person shooter games was beneath him. But Sam had seen the way that Dean watched the group play.

At first, he’d sat on the edge of his seat, silently observing. Then after a couple of months of watching, he’d started offering suggestions and commentary too. A couple of times when they’d all been uncertain about a rule and had been about to pull up the player's manual to check, Dean had beat them to it and started spouting out rules. Verbatim. From memory.

Sam was pretty sure that if Dean had less pride that he’d have joined their games a long time ago. Or maybe if Dean hadn’t made such a big deal about DnD being for losers when Sam had started planning his first campaign... Still, Sam couldn’t help but bite back a smile as Dean breezed through filling out the character sheet that Chuck had passed him. Charlie had passed him her laptop with DnD and beyond pulled up on it in case he needed to look anything up, but he barely used it.

“Done,” Dean said triumphantly, setting aside his sheet.

“Well, introduce us to your character,” Charlie said.

“Right,” and Dean seemed to lose some of his confidence as he glanced down at the page, “Uh, his name is Jensen, he’s a human fighter.”

“And?”

“I don’t know man, what do you want me to say?”

Charlie patted his arm encouragingly, “Here, I’ll show you how it’s done.” She gestured grandly and put on an over the top southern accent, “Howdy y'all, I’m Felicia, I’m a tiefling artificer and I used to work making magical weapons for the government until I found out they were corrupt. Now I’m on the run because I have valuable information and they want me dead.”

“Charlie,” Chuck sighed, “You can’t overthrow the government in every campaign.”

“That’s what you think,” Charlie said with a wink.

“Are you going to use that accent the whole time?” Cas asked.

“Of course. Unless I forget. Now Dean, what’s your character's backstory.”

“He doesn’t have one,” Dean said, crossing his arms.

“Oh yes he does,” Gabriel said pointing to Dean’s character sheet, “You filled up the box.”

“It’s stupid.”

“Dean,” Sam said, “It’s really not a big deal, we all have dumb character backstories. It’s half the fun.”

Dean sighed. “So, Jensen, right. He’s a cowboy, or whatever. He’s been fighting demons his whole life because his mother was killed by one.” He paused and looked out at the table, “And I’m not doing some dumbass character voice. So yeah.”

“See, that’s a good one.” Gabriel said, nodding solemnly, “Dead mothers are a classic.”

A look passed between Sam and Dean.

And Dean and Jo.

And Sam and Charlie.

The Winchester brothers didn’t exactly go around shouting from the rooftops that their mother was dead, but Gabriel probably knew, in that back of the mind sort of way. Still, he wasn’t a very sensitive person at the best of times. Sam was sure he hadn’t meant anything by it. But that sentence, it still made him wince, just a little.

And Dean; Dean who could actually remember their mom, Dean who had someone to miss, he just went very quiet.

After a moment he pushed back from the table, “You know what, I came down here to order you guys some food. What do you want? Chinese? Is Chinese good with everyone?”

There was a loud murmur of assent, then all around the table, every player rifled through backpacks and pockets and forked over whatever they could contribute to the bill.

The first couple of times they’d done it Dean had tried not to accept the money, but Sam had told his friends not to take no for an answer.  
Sam knew that getting them takeout was Dean’s way of trying to make Sam’s life a little more normal. He was trying to be the parent that got food for all of Sam’s friends without being asked and thinking about the bill. And as nice as it was, Sam knew that Dean couldn’t afford takeout for six or more people every week. Especially when those same people were constantly over at their house, helping themselves to the chips and sodas and snacks that Dean bought.

Dean shouldn’t have had to provide for the two of them in the first place, and Sam was going to make damn sure that if Dean went around buying food for his friends, that they could at least cover the tip.

Dean collected the money absently and headed up the stairs pulling out his phone.

“What was that about?” Gabriel asked.

Jo elbowed him roughly. “Asshole.”

“What?!” Gabriel asked.

“Dead mothers are a classic,” Jo mimicked, “Seriously dude, read the room.”

Gabriel’s eyes went wide, and his mouth formed a small _Oh_. He turned to Sam, “Shit man. I’m sorry.”

“It’s fine,” Sam said, “It was a long time ago.”

“You could apologize to me too,” Jo said, crossing her arms. She’d lost her dad only a few years back.

“I’m sorry Jo.”

“I’m going to check on Dean,” she said, standing up and moving toward the stairs, but before she could reach them Dean was coming back down.

“Egg rolls?” He mouthed at the group. And Charlie nodded, “Alright, a side of egg rolls, and can we get an order of the kung pao chicken too? Thanks.” Then he gave their address and hung up. “Food’s on its way. We should play I guess.”

***

As they ate their Chinese food they went around and finished their character introductions.

Sam’s character was a warlock named Jared on a search for his missing father, and everything about Sam’s character from the ridiculously average name, to his class choice, seemed to piss off Chuck. Meanwhile, Cas’s character was a cleric aasimar named Misha who’d fallen out of favor with his godly patron. This, if it was possible, made Chuck even angrier, because now he had to come up with a whole deity centric mythology, just for the benefit of Cas’s character.

Jo’s character was a former Saloon girl turned ranger named Alona, and before she had even finished speaking, Dean was asking her if her character was hot, “yes,” and if Jensen had a shot with her, “I’ll kill you.”

Kevin’s character was a wizard named Osric, and by the time Chuck made it around to the Wild West Wizard, he was already too desensitized to care.

Gabriel’s gnome was a bard who carried around a magic flute and to top it all off, he’d decided to name this masterpiece of a character Dick.

Chuck looked about ready to tear his campaign notes to shreds.

He stood up from the table and grabbed his notebook. “Okay, okay. I just need to make a few adjustments in light of new information,” and he headed up the stairs.

The table stared at each other.

“Were we being too mean?” Charlie asked, “I mean, I know he’s not good about us disrespecting his creative vision or whatever, but I just wanted to be a tiefling.”

“We shouldn’t have let him DM.” Gabriel said, shaking his head, “DMs have to be flexible and just our characters are giving him an aneurysm.”

“Come on guys,” Sam said with a frown, “He really wanted to run this campaign, we should stop being dicks.”

“Yeah, alright _Jared_.” Dean grinned.

“What?! It’s the wild west, not high fantasy, it’s not that bad of a name choice.”

“No cowboy is named Jared.”

“What should I have named him? Cordell?”

“ _Maybe._ Better than _Jared_.”

Then Chuck came back down the stairs. “Okay, so I think I can make this all work, I just have to rework some things. We’ll start playing next week.”

“Next week?” Dean asked incredulously.

“I have to work in your character backstories, but I think this could be good. I have some ideas.”

“Alright then,” Gabriel said standing up, “Cassie and I should probably be going. He’s got homework to do, I’ve got mailboxes to smash. Let’s go cuz.”

Cas reluctantly stood up from the table, “It was nice to meet you both,” He said directing his words and Dean and Jo, “And I’m sorry about your mom Dean.”

Dean blinked at him, "... Thanks, man.”

After they were out of the house Dean turned to the group. “Man, that guy is weird.”

“He’s really nice Dean.” Charlie said, shooting him a look, “His people skills just aren’t that great.”

“I liked him too.” Jo offered, “He seems sweet.”

Dean snorted, “You just think that because he’s cute or whatever.”

Jo rolled her eyes at him, “You know Dean, just because guys think with their dicks doesn’t mean girls make up their minds that way.”

"Who said I was thinking with my dick?" 

Jo dropped into a half decent imitation of Dean's voice, "I don't like the guy, seems sketchy, cute tho."

Dean scoffed. And as Dean and Charlie and Kevin and Jo prattled on, Sam slouched back in his chair, observing. His brother and his best friends all around one table, Dean's relaxed smile, Charlie's easy laugh. Dean always seemed to be stressed lately, but right now, he actually seemed almost okay.

_This,_ Sam thought to himself, _This had been a great idea._

**Notes for the Chapter:**

> Hey, thanks for tuning in for this first chapter! I have a lot of plans for this fic, so don't be surprised if the total number of parts goes up. I'm a college student and I have no discipline, so my update schedule might be... a little erratic.
> 
> Anyway, this fic is going to be coming of age//slice of life//slowburn Destiel, with a probably unhealthy heaping of family drama. If that sounds like your type of fic, I hope you stick around to read it. <3


	2. Dad's on a Hunting Trip…

**Notes for the Chapter:**

> trigger warnings:
> 
> mentions of alcohol abuse...
> 
> and John Winchester

Castiel Novak did not know what to make of Dean Winchester. 

He was not very good at working out people in general. Sometimes he felt like he’d been born with a chip missing. Where everyone else seemed to resonate on the same social frequency, Cas had to work, and observe, and mimic people to tap into it. It was usually easier when the person fit into an easy to suss out box, or when Cas shared a common interest with them. With Sam’s group, it was easy, they all wore their interests on their sleeves, and they’d liked Cas right away when he hadn’t judged them for it. But with Dean, things were a little more complicated.

When he’d met him at that first campaign session Dean hadn't made the best first impression on Cas. He'd swaggered and made fun of Sam’s friends and the things they all liked. But then there was the Dean that had just wanted to play the Western campaign and the Dean who'd been upset enough that he'd left the room when Gabriel had mentioned his mom.

None of those Dean Winchesters fit together in his head, and now he was mentally adding another one to the pile as he watched Dean whistling and vacuuming the living room carpet.

“What did you put for question eleven?” Sam shouted over the roar of the vacuum.

Cas turned back to his AP Government study guide, “It’s A.”

“Not C?” Sam asked.

“No, I’m pretty sure it’s A,” Cas said, but he was watching Dean out of the corner of his eye again.

The Winchester house was relentlessly clean. The furniture was sort of shabby, and the house itself was small and outdated, but there wasn’t so much as a speck of dust on the coffee table. Cas’s house had always been clean like that too, but he and his sister Claire had only really helped out with the chores when their parents had forced them to.

Cas had been over twice since the campaign the previous Friday to study with Sam, and he hadn’t seen Sam and Dean’s dad at all either time. And yet the first time Dean had spent most of the evening doing dishes and making dinner, and this time he’d started vacuuming the entire house. Cas didn’t get it. He’d never met a single person his age who vacuumed voluntarily, and Dean, in his faded jeans and wrinkled green army-surplus jacket hardly looked like a neat freak.

“Cas?” Sam poked him in the shoulder with his pencil eraser, “You seem distracted, wanna take a snack break?”

Cas nodded in agreement.

As the two of them headed toward the kitchen, Dean turned off the vacuum for a moment to call out, “Sammy, grab me a soda?”

Sam gave Dean a thumbs up, and as he opened the fridge Dean called out again, “NOT a diet one.”

“Yeah, yeah,” Sam mumbled, “You’re going to give yourself a heart attack you know,” he said as he handed his brother the soda.

“It’s my right as an American to die young and of heart disease.” Dean said, and he tipped his soda in Cas’s direction and winked, “Am I right Cas?”

When Cas didn’t answer Dean shook his head and went back to vacuuming.

And that was another thing Cas didn’t get. From Sam, from Gabriel, from basically the entire group, he had heard overwhelmingly that Dean was this annoyingly masculine person. That he liked beer, and classic rock, and Saturdays with the boys. That he’d blown up at a guy at his high school who’d asked him if he was gay, and that he probably would have died of scurvy by now without Sam around to convince him to force down the occasional vegetable.

And Cas could see that version of Dean, but when he combined it with all of the other Deans he’d observed, it felt like something he was hiding behind. The caricature superimposed over the truth. Not that he had any idea what that truth was supposed to be.

He and Sam were eating grapes (because Sam insisted that they were “brain food”) and were chatting about the latest comic book Sam was reading (as in, Sam talked, and Cas politely asked questions whenever Sam paused for air) when the doorbell rang. Cas watched as Dean set down the vacuum and went to answer it.

“Bobby,” Dean said, “What are you doing here?” and Cas could hear the smile in his voice. After he’d heard Bobby’s name Sam had wasted no time making his way over to the door.

“Hey Bobby,” Sam said, and Bobby, who was wearing a baseball cap and a flannel, gave each boy a hug.

“Thought I’d stop by on my way home from work. I haven't seen you boys in a while.”

“We’ve missed you,” Sam said, shoving his hands in his pockets.

“Yeah, yeah.” He waved them off, “I’ve got groceries in the car for you, help me carry them in.”

“You’ve got it,” Sam said, and he headed out to the curb.

“You really didn’t have to do that,” Dean said, shaking his head.

“Yes, I did.”

“Do you want help bringing in the groceries?” Cas asked. He was beginning to feel awkward, just sitting at the table with his grapes.

“Yeah, thanks man, that’d be great,” Dean said. As they walked out to the car together Dean made the necessary introductions, “Bobby this is Cas Novak, He goes to school with Sam. Cas, Bobby Singer.” He said, pointing between the two of them.

“Nice to meet you, Mr. Singer.”

“Bobby’s fine,” he said, nodding at Cas.

With all of them working together they were able to get the groceries inside in a single trip, but once they’d set all of the bags down Cas had quietly excused himself, headed down the hall to the bathroom, and shut the door. He didn’t actually have to go, but he was having that familiar unease in his chest that he’d cultivated over a lifetime of being weird. It was a clenching in his gut that said, _that might be a weird thing to say,_ or _you’re doing something wrong in this social situation right now._ The feeling wasn’t always right, but Cas had learned that if he just stayed quiet or excused himself from the situation when he felt it, that interactions usually went better for him in the long run.

Being around these boys and Bobby, it felt like intruding on a private moment. If Sam and Dean hadn’t called Bobby by name, he might’ve assumed that he was their dad. They seemed so happy to see him, and every bone in Cas’s body told him that he was an unnecessary presence in that dynamic.

He stood there for a while looking in the mirror, and he was about to head back to the kitchen when he heard Bobby’s voice filtering down the hall and his tone stopped Cas short.

“So where’s your old man at?” Bobby asked. His words were low and steady, but vaguely comforting. Like the topic was a stray cat he didn’t want to scare off.

“He’s uh,” Dean hesitated, “On a hunting trip actually.”

“Is he now.” Bobby said suspiciously, “Another one?”

“It’s fine Bobby.”

“How long’s he been gone?”

“Not long.”

“Dean.”

“Eight days.”

Bobby sighed audibly, “And he’s been keeping in touch?” If either of the boys said anything Cas couldn’t hear it. “Goddamn it, he can't pull this shit. When did you last hear from him?”

“He texted me on Saturday morning,” Sam said quietly.

“He did?” Dean asked, and Cas could tell that that was news to him.

“So he hasn’t contacted either of you at all for five days?” 

“Bobby it’s fine.” And Cas could hear the weariness in Dean’s voice, “He’s gone radio silent for longer before.”

“Like hell it’s fine!”

“I’m eighteen Bobby, It’s not like we need him around anyway! We do fine on our own.”

Bobby’s tone softened, “I’m not saying you can’t take care of yourselves Dean, but you shouldn’t have to. Sam’s only sixteen. For two more years, John is legally responsible for his well-being. He can’t just disappear like this. I’m going to give him a call.”

“Bobby, don’t.”

“I’m calling him Dean, and if you don’t hear from him tonight, you both come stay at my place until he gets back home, alright?”

“Yeah. Alright.” Dean agreed reluctantly.

Cas waited in the bathroom for a couple more minutes until he heard the front door shut and saw Bobby’s pickup driving down the street. He crept back into the kitchen cautiously. Sam turned to look at him. Dean was sitting at the kitchen table, his head in his hands.

“So, I’m guessing you heard all of that,” Sam said, shaking his head embarrassedly.

“Most of it.”

“Sorry man, family stuff. It’s uh… complicated.”

“Don’t worry,” Cas said softly, “I get complicated family stuff.”

Sam looked relieved.

“So your dad, he hunts?” Cas asked, looking for a way to shift the conversation.

“Yeah,” Sam replied.

“What sort of animals does he… uh?”

“IPAs mostly,” Dean said sardonically.

“Dean.” Sam hissed.

“What?” Dean looked up and flashed a wry smile, “Hunting trip. Bender. Same thing right?” Then he stood up and shook his head angrily, walked down the hallway to his room, and closed the door.

A beat of silence fell between the two boys until Sam finally said, “Our dad, he’s not… he’s not all bad, but ever since our mom died, he’s had some issues.”

Cas nodded.

“And when it gets to be too much for him, he just leaves. Business trips, hunting trips, I think sometimes he does actually hunt, but mostly it boils down to him disappearing somewhere to drink. And Dean, uh-”

“Stop talking about me Sammy!” Dean called, his voice muffled through the walls.

Sam rolled his eyes and lowered his voice, “Sorry, he uh- a lot of this shit, it ends up falling on him, you know?

***

Cas did know, and he thought about Sam’s words as Gabriel drove him home.

When you were an older sibling there were certain things you just didn’t get to do. Especially when you had shitty parents.

You had to be the one to take the fall. The one to pick up the slack.

You didn’t get to be selfish. You didn’t get to disappear… Cas was a terrible brother. But he did understand Dean better now, at any rate.

He was the kind of boy who vacuumed the living room without being asked because if he didn’t do it, no one else would.

**Notes for the Chapter:**

> Thanks for reading, new chapter coming next ?Friday?


	3. An Angel of the Lord Walks into a Bar

**Notes for the Chapter:**

> long chapter, buckle up.

It wasn’t bad as D&D campaigns went. Dean could almost even admit to himself that it was more fun playing than it was leaning over Sam’s shoulder and making snide comments. 

Almost.

The crew had set up again in the combination storage room and black mold factory that was the Winchester basement, and Chuck had been leading them through what so far, wasn’t a totally lame campaign.

Over the course of the week, Chuck had apparently worked with Charlie, Kevin, and Cas to reskin their characters into something that fit his world-building a little better. Charlie’s tiefling had been workshopped into a morally gray demon, and Kevin’s wizard had a more “modern-day witch” energy.

Gabriel had refused to budge on his gnome.

Still, everyone was having a pretty good time. Dean had gotten to interrogate and kill a demon and flirt insufferably with Jo’s character as Jo threatened to stab him in real life if he kept it up. Chuck had even hinted at a quest that they’d have to embark on (getting a Demon slaying gun called the Colt to avenge the death of Dean’s mother). All and all it was going pretty well. He did feel a little bad for Cas though.

Chuck had introduced most of the group all at once, having them take a minor job together, but he hadn’t introduced Cas’s character Misha at all yet. Cas hadn’t exactly complained about it like Dean knew that he would’ve if it were him, but he’d basically been silent for the majority of the campaign, minus a muttered comment to Charlie here and there.

Now their first real session was coming to a close, and the assorted crew of cowboys and wizards and gnomes sat around a table in a rundown old bar. Chuck's descriptors weren’t all that specific, but Dean had watched Tombstone enough times to paint himself a picture of muted tones, shady characters gambling in the corner, and top-shelf whiskey in crystal tumblers.

Chuck described the pretty waitress that came by to take their drink order, and Dean couldn’t help himself.

“Jensen hits on her.”

“Of course he does,” Sam said, rolling his eyes.

“Are you going to flirt with every NPC in this campaign? You know there are girls out in the real world that aren’t just Chuck making a high-pitched voice for you to get it on with.” Gabriel asked with faux concern.

“Isn’t that the point of the game?” Dean asked sweetly, “Nerds hit on made-up elf girls to forget that real girls won’t talk to them?”

Sam looked exasperated, but Gabriel just smiled sharply and said, “I’m just saying Deano, if you hit on anything with boobs, people are going to start to think you’re overcompensating for something.”

Dean snorted, “Yeah, yeah, whatever,” He turned his attention back to Chuck, “Can I roll charisma or what.”

“Go for it.”

Dean gave the die a cursory shake, and it fell onto the table with a disappointing clunk.

Jo laughed, “That, is a crit fail.”

“Shut up.”

“You’ve rolled pretty well so far,” Sam said with a suppressed smile, “it was bound to happen sometime.”

“Yeah, well, what happens now?”

Chuck contemplated for a moment, “Uh, you try to talk to her, and you get halfway through a pickup line, and then accidentally knock your glass of water off the table and it spills onto your lap.”

“Well, that’s just great.”

“She laughs at you.”

“Little does she know, Jensen’s into that,” Gabriel said waggling his eyebrows.

Dean elbowed him, probably a little harder than necessary.

“I like that in this universe Dean has no game,” Charlie said with a laugh.

“Hey I have great charisma stats, I just rolled like shit.”

“Just saying, between Alona and that server, you’re batting zero.”

“Yeah yeah,” Dean shrugged, waving her off, “In the real world I’ve got all of you beat.”

“I don’t know Dean, I’ve bitches.” Charlie said solemnly.

Dean shook his head with a rye smile, “Yeah, you do Red.”

"Guys," Sam said, clearing his throat, “Can we get off of Dean’s dating life and back to the game?”

“Whatever you want to do Sammy.”

“Okay, so Jared’s going to turn to the group and say, ‘So we have to get to Deadwood and find the Colt to kill Azazel. We should ask around, maybe someone here knows more.’”

“'Yeah, you do that,'” Jo replied as Alona, “I’m going to finish my drink.”

“Alright,” Sam said, “Jared stands up from the table and goes to look around.”

Then Chuck smiled a concerning kind of smile, “Alright. You stand up, but as you do, you stop in your tracks. Above your heads the lights flicker out, one by one, and then come back on again, glow brighter and burst, the bulbs exploding in showers of sparks.”

“Well, that’s fucking ideal.” Dean deadpanned.

“—Your drinks shake on your table and it takes a moment for you to realize that it’s not just the table that’s shaking, but the ground itself. A sudden piercing whine splits the air: Everyone roll a constitution saving throw.”

The group exchanged looks.

Dean blew on his D20 before he rolled it. He was finding that, for a guy who’d never really played D&D before, he had a lot of dice-related superstitions, at least when the roll was an important one. So far it seemed to be working out for him. A fifteen sat prettily on the table.

Most of the group didn’t get quite so lucky, Jo rolled a three, Gabriel a six, and Kevin a five.

“Alona, Dick, and Osric all sink to the floor covering their ears. Jensen, Jared, and Felicia hold their ground, but barely, the noise is piercing, and between the moving ground and flashing lights, you all feel a little sick. I want you three to roll initiative with disadvantage.” 

Then Chuck had them all roll initiative.

Dean’s first roll was a nineteen, and he let out a string of curses. He doubted his luck will hold for his second roll. In the end, though, he managed to pull a respectable sixteen with his modifiers. Sam pulled a ten, and Charlie rolled a four.

Chuck rolled and then sighed, “Alright Dean. You have first initiative. Suddenly, a man appears in a burst of light and sparks. He starts to materialize in front of you—”

“So, I’m going to run at him and stab him.”

“Dean you don’t even know what the hell is going on here yet are you sure you want to—”

“I rolled a non-nat twenty, does that hit?”

“Yes. That hits. So what do you do?”

“I get a running start, and I just stab him, right in the heart.”

“The man looks down at the knife, looks back up at you, and pulls the knife out like it’s nothing.” Then Chuck turned to Cas, “You’re up next, what do you want to do.”

Dean turned to look at Cas who had a tiny half-smile on his face. We watched as Cas turned his face down towards his lap and Dean realized that he was writing something.

“Have you been passing notes with Chuck this whole time?” Dean asked.

“Not the _whole_ time.” Cas said as he passed the note under the table to Chuck.

Dean glared at him.

“Roll for that,” Chuck said with a smile, and he and Cas shared a conspiratorial look.

“It’s a… twenty-two. I throw out my arm, and Jensen flies backward across the room.”

“Oh come on! How the fuck is that possible?” Dean asked, looking down at the seventeen Cas rolled.

“‘Who are you?’ Jared askes.”

“‘My name is Misha, I’m an angel of the lord.’”

“What kind of a name is Misha for an angel?” Sam asked aloud.

“What kind of name is Jared for a cowboy?” Dean replied before Cas could answer.

“Shut up man, it’s a good name.”

“‘My name is Misha, I’m an angel of the lord.’” Cas repeated again, “‘Jensen, Jared, Felicia, Osric, Alona, and Richard—”

“It’s just Dick,” Gabriel threw in, “It’s not short for anything.”

“Your character’s full name is Dic—”

“GUYS,” Chuck interrupted, “Let Cas finish his sentence.”

“Right,” Cas said, getting himself back on track, “‘I’ve been sent by God to tell you that Lucifer is rising and you’re humanity's last hope.’”

The group looked around at each other, and Dean shared a meaningful look with Sam, “So that’s some bullshit right? We’re all on the same page here? That’s bullshit?” Dean asked.

“I want to try and do a sneak attack against him while he’s monologuing,” Sam said.

“You can try… roll stealth.”

Sam got a nineteen. “So I sneak up behind Misha and—”

“He flicks his hand and sends you flying across the room without even looking at you,” Chuck finishes.

“Come on man, that’s not fair, you didn’t even roll for him!”

“He’s an angel Sam, I jacked his stats. Stop trying to kill him, he’s supposed to join your party!”

“Just because he beams down here all Princess Leia style doesn’t mean we have to trust him,” Dean said, crossing his arms.

“Princess Leia style?” Cas shot Dean a puzzled look which Dean returned.

“Help me Obi Wan Kenobi, you’re my only hope?” He said, trying to clarify.

“I don’t understand that reference.”

“Star Wars dude, _A New Hope?_ ”

Cas shook his head and Dean stared. “Dude—”

“‘So you just expect us to believe you’re an angel?’” Charlie said as Felicia.

“”Yes.’” Cas’s character replied blandly, “‘There are much bigger threats on the horizon than the demon Azazel, and you must travel to find the colt and use it for a higher purpose.”

“So you want us to find a magic gun to save the world from Satan?” Dean asked.

“‘Yes.’”

***

The campaign had run far later than usual and all around Dean the members of the campaign were cleaning up to leave. Chuck was sweeping his little dolls back into his bag and getting his notes together, Charlie and Kevin were putting away the folding chairs, and Sam was heading upstairs to toss the pizza boxes.

The session had gone well, it had certainly been dramatic enough, but one thought was still nagging at Dean. “Cas,” Dean asked, grabbing his attention. Cas looked surprised that Dean was speaking to him, his brows knitting together. “Have you really never seen Star Wars? Like ever? None of the movies?”

“Uncle Zach and Aunt Naomi probably think that Lucas Films is a harbinger of the devil.” Gabriel snorted from where he sat just behind Dean. Unlike everyone else, Gabriel hadn’t bothered helping clean up. He was still sitting in the only remaining folding chair, his feet propped up on the card table.

Cas shot a cool look at his cousin and then said, “My parents are… pretty strict, so there are a lot of movies I haven’t seen.” then he forced a small smile and shrugged lightly. Like it didn’t really matter. 

Dean couldn’t help but picture Cas as a child, watching movies that were the equivalent of Christian rock and eating, like, communion wafers or something.

“Well, we’ve got all of the movies. You can come over and watch them sometime if you ever want to see them.” Dean said with a shrug.

“When?”

“Huh?”

“When would we watch Star Wars?” Cas asked.

“Oh, uh…”

And Dean was a little thrown. He’d been offering more in the obligatory “You’ll owe me a favor'' sort of sense. It wasn’t an invitation he’d really expected Cas to collect on, and especially not right away. But that seemed to have flown way over Cas’s head.

And then there was the “we” of that statement. If Cas did want to watch Star Wars at their house, Dean’d figured that that was something for Sam to deal with. Dean hadn’t exactly pictured him and Cas getting all cozy on the couch for a little movie night together. He didn’t really know Cas, and in the handful of times he’d seen him, they hadn’t ever had to carry a conversation or hang out just the two of them.

As much as Cas deserved to experience lightsabers and AT-AT’s, making it through a movie night, just the two of them, would’ve probably been one of the more awkward things Dean had ever done.  
He thought about brushing him off, but when he looked at Cas there was something in his expression— Hope maybe? Or excitement? The guy was so self-contained it was hard to tell— and Dean couldn’t do it. Dean cupped his hands around his mouth and called across the room, “Hey Charlie! Cas hasn’t seen Star Wars.”

The sentence had its desired effect.

Charlie spun around where she was standing and gaped at them, “Oh my God Cas, I thought you were kidding!” she started to make her way across the room and Cas shifted uncomfortably from foot to foot. “We’re making him watch it right?” Charlie asked.

“Hell yeah, we are. You got anything else going on tonight Cas?”

“Not really.” Cas said after a moment of contemplation, “Gabriel would have to give me a ride home.”

“Gabe?” Dean asked, elbowing him.

“Eh, sorry, no can do Deano, I need to get home and start my homework so I don’t,” and he put air quotes around the next bit, “' _fail out of Spanish.'_ So I can’t be anyone’s chauffeur tonight.”

The implication that Gabriel wasn’t already failing all of his classes startled Dean, but he forced himself not to make a jab about it and turned back to Cas, “That’s no big deal, I’ll just drive you home after. I’ve got a car.”

“Dive me too?” Charlie asked, poking Dean in the arm.

“Yeah, no problem, I’ve got you.”

“That’d be great then,” and Cas smiled. Like really smiled.

It wasn’t a look that Dean had ever seen on him before. Cas had such a serious face, his brow always furrowed, his mouth a hardline, but looking at him then, you’d never have known it. His eyes were bright and genuine, and suddenly Dean didn’t feel so weird about watching a movie with the guy. Or maybe he felt weirder about it, he wasn’t sure.

“Cool. So. We’ll watch a movie then.”

***

In the end, Charlie, Jo, and Cas had all ended up staying, and with Sam, it made for a pretty crowded viewing experience.

They had all spent a whole ten minutes discussing if they should watch the films chronologically plotwise, or in the order they came out. Sam had suggested that watching the movies following the timeline would be less confusing for Cas. Jo had rooted for the prequels as well because they were more fun to make fun of and she was a firm believer in talking over movies. But Dean, who didn’t want Cas to think that all the Star Wars movies sucked as bad as _Phantom Menace_ , and Charlie who was a series purest, had been in favor of _A New Hope_ first, just on principle. After a heated game of rock paper scissor, chronological order had won out.

After that, they’d all clambered to claim seats. Jo had grabbed the big armchair in the corner and was laying across it, her feet dangling over the armrest, and everyone else had ended up squeezed onto the couch.

Sam was taking up way more space than seemed fair, and it left Dean, Cas, and Charlie all pretty much shoulder to shoulder. It wouldn’t have even been so bad if it was Charlie that’d ended up sitting next to him, but instead, it was Cas. Dean had spent half of the movie awkwardly elbowing Cas on accident and then trying to shove closer to the armrest to give the guy more space, and the other half of the movie telling Cas to shut up.

Cas as it turned out, was not the kind of person who could just accept information as it was being conveyed on screen, and every two minutes or so he would lean over to Dean and whisper, “Who’s that?” or, “What’s an X-Wing?” or, “How does the force work?” and Dean would have to hiss back, “Just be quiet and watch.”

After the tenth or so time that Dean did this, Cas protested, “But you guys are talking too.”

And it was true, they were.

Jo made snide comments about the kid playing Anakin every time he was on screen, and Charlie would get up and pause the movie every so often to inform the group of a meta-theory she’d read on Tumblr that the scene had reminded her of.

“See, this is what I don’t get,” Jo said as Padme knelt down to speak to Anakin at eye level on the screen. “You mean to tell me that _Natalie Portman_ ends up with that kid when Ewan McGregor is right there?”

Cas’s brow crinkled in concern, “Padme dates that child?”

“In the next movie there’s a time skip,” Sam explained, “Anakin’s like nineteen then.”

“It’s still so weird, like, she’s known him since he was nine.”

“To be fair,” Charlie offered, “She’s only supposed to be fourteen.”

“Still!” Jo said, crossing her arms. “Say you’re fourteen, who do you have a crush on, the nine-year-old? Or the super hot Jedi?”

“Jo’s right,” Cas replied solemnly, “Obi-Wan Kenobi makes way more sense.” When Dean stared at him he clarified, “Obi-Wan is much more attractive than the child.”

Dean snorted at that, “Uh yeah, okay. Just wait until you see Hayden Christensen in the next one.”

Jo laughed aloud.

“No, really,” Dean said, standing up, “We’re taking a vote.” He crossed the room dug haphazardly through their stacks of DVDs until he came up with _Revenge of the Sith_ , “Joanna Beth, you look at this, and then look me in the eye and tell me that Ewan McGregor is hotter than Hayden Christensen.”

She looked Dean dead in the eye, “Ewan McGregor is hotter than Hayden Christensen.”

Dean shook his head in disgust and passed the movie case to Cas, who stared at it for a while and then pointed to Hayden Christensen.

“Ha!” Dean said grinning, “That's two for Christensen, Charlie?”

Charlie glanced at the DVD and shrugged, “I don’t really know, they aren’t really my type if you know what I mean.” She punctuated it with a little joking smirk but Dean was just annoyed.

“I have an opinion, and they’re not exactly my type either,” Dean said defensively. It wasn’t like you needed to find a guy _attractive_ to know that he was objectively hot.

“Could’ve fooled me,” Jo muttered into her glass of diet coke.

Dean shot her a glare, but before he could ask her what the hell that was supposed to mean Sam intervened, “I think Ewan’s hotter. It’s a tie. Great, now that that’s settled can we get back to watching the movie?”

And Dean, reluctantly, fell back into his seat with a huff as Charlie unpaused the movie.

***

An hour later as the credits rolled Dean stood up again, stretched, and walked over to grab his car keys off of the window ledge by the front door. “I should probably get you two home,” he said, turning to Cas and Charlie.

Charlie yawned, but got to her feet, “I call shotgun,” She said nudging Cas’s ankle.

Cas nodded stiffly and slowly stood up.

“Hey,” Jo said, coming over to Dean, “I’m heading out too.”

“See you, Jo,” he said, giving her a quick hug goodbye before she headed out to her car. “Sammy,” He said, shaking Sam’s shoulder. He’d fallen asleep before the movie had ended. “Movie’s over, get to bed.”

Sam grunted in response.

Dean sighed and shook his head, “Alright you two, let’s get going,” and the three of them headed out the back door and to the detached garage. 

Inside sat Baby, Dean’s pride and joy.

It had been his dad’s car until Dean had turned sixteen. He’d always loved it, but he’d never expected his dad to give it up. In fact, he’d never really expected to get a car from his dad at all.

Sam certainly hadn’t got one when he'd turned sixteen last spring.

But Dean figured the circumstances had been different when Dean had sixteen. John had been around more, but whenever he did leave, he was leaving behind a fifteen-year-old and a thirteen-year-old, which was a very different thing than an eighteen-year-old high school graduate with a job, and a sixteen-year-old college-bound high school junior. They couldn’t drive in an emergency, and Dean couldn’t work much with school and everything. Sammy hadn’t even had his own cell phone back then. John usually left them some cash, but it was never enough to get by on long-term. And sometimes, what John promised would only be a few nights did end up being long-term.

Dean had spent most of his freshman and sophomore years of high school putting whatever money he could spare, after groceries and expenses, towards a used car fund. It had been going pretty well too. He’d been bookmarking cheap used cars on Craigslist, Bobby was teaching him to drive, and with his dad still usually paying the bills every month, Dean had even managed to save up a few hundred dollars working at the shop.

Then Sam had broken his leg, and John had been out of town, and Dean had had to pay the deductible on their insurance out of pocket. And all at once, he was back to zero.

It hadn’t mattered in the end though. He’d woken up the morning of his sixteenth birthday to see a black pickup he’d never seen before parked in their driveway, his dad home and sitting at the kitchen table, and a pie from a nearby diner in the fridge. John had given him a smile that almost read as proud.

“I got a great deal on a new truck,” He’d said, hitting Dean with a steady gaze, “And it got me thinking, a man needs a car of his own…” And he’d sent the keys to Baby sliding across the table to Dean, just like that. There hadn’t been much fanfare to it, that wasn’t John Winchester’s style. Still, it was hands down the best birthday present John had ever given him. Now that he thought about it, it was probably the best birthday he’d ever had with his dad involved, period.

Charlie ran around to the passenger’s side of the car and Cas climbed into the backseat.

Dean watched Cas’s face in the rearview mirror as he took it all in.

Showing people Baby sometimes felt like showing them a piece of himself. The cracked leather seats, the lingering smell of cigarette smoke from when it had been John’s. The car comforted him in ways he couldn’t explain, and he wanted everyone else to understand that too.

Cas had noticed that Dean was watching him, and he stared back for a moment before realizing that Dean was waiting on him to say something “This is an _old_ car,” he said finally.

Dean glared. “I think you mean an _awesome_ car. This beauty has a 327 Engine and a Four Barrel Carburetor.”

Cas stared at him blankly, “Is that… good? I don’t know anything about cars.”

“Yeah, well,” And Dean tried to remember why he cared at all what any of Sam’s stupid friends thought of his car, “The point is, she's not old. She’s vintage. And she runs perfectly.”

Cas was still staring at him, and even after Dean looked away, he could feel it on the back of his neck. It was… disquieting. Dean started the car and then sat there trying to remember what he was supposed to be doing when a flicker of motion in the corner of his vision caught his eye.

Charlie was fiddling with the radio.

Dean instinctively batted her hand away, “Nope. You know the rules, driver picks the music.”

“Oh come on Dean!” Charlie said indignantly, “Let me pick, just this once.”

Dean had let Charlie pick the music once, he remembered it perfectly. It had been her fourteenth birthday. Dean had only had the car for a couple of months. He’d let her pick the music, and she’d spent five minutes scanning channels until she’d found a radio station playing an hour of sea shanties. Dean had not been in a sea shanty sort of mood. 

Dean had _never_ been in a sea shanty sort of mood.

He stuck out his hand and Charlie sighed and grabbed the box of cassette tapes at her feet. Dean rifled through it and pulled out an Iron Maiden tape.

Once he had music pumping through the speakers the drive to Charlie’s was nothing. She only lived seven or so minutes away, and he’d driven her home half a million times, so he knew her address by heart.

As he pulled into her driveway Charlie grabbed up her book bag and slung it over her shoulder. “See you next week Dean,” She said, and she leaned over the consul to give him a one-armed hug.

Dean murmured back a quick, “See you kiddo,” and she gave his shoulder a squeeze.

“And I’ll see you on Monday Cas!” she added, then she was outside and heading to her front door. She looked back over her shoulder one last time and called, “Later losers!” Before disappearing into her house.

Then it was just him and Cas. He looked at the guy in the mirror again. His dark hair was a mess and he was staring unflinchingly back at Dean.

“So uh, what’s your address?”

Cas hesitated for a moment, “I’m actually living with Gabriel and his dad this year.”

Dean blinked. He’d seen Gabriel driving Cas everywhere, but he’d just figured that Gabe was being an uncharacteristically good cousin. “Well, I gotta level with you man. I don’t know where Gabriel lives either.” 

Cas rattled off the address and Dean plugged it into his phone without comment.

 _Cas is living with Gabriel,_ Dean thought as he pulled out of Charlie’s driveway. And he was a little tempted, okay _a lot_ tempted, to ask for the story behind that. But he couldn’t think of a scenario where someone would choose to live with Gabriel if they had a better option at their disposal, and he didn’t want to dredge up anything bad. Gabriel and Cas hadn’t spoken about Cas’s parents in the past tense, but for all he knew, they’d died recently, or something else equally as shitty had happened.

“So is that how you ended up starting at the high school this year?” Dean asked finally instead. He figured it danced around the subject of why well enough.

Still, Cas answered the question with a simple, “Yes.” Like he had no interest in elaborating any further.

They drove in an awkward silence for a couple more blocks before the oppressive silence forced out another half-baked conversation attempt.

“I really liked the movie,” Cas said, and Dean snorted a laugh.

“You don’t have to lie. _The Phantom Menace_ is pretty much the worst one.”

“No really. It was fun.” Cas said, and his hands fidgeted restlessly with the cuffs of his shirt sleeves, “I’d like to watch the rest of them.”

“Yeah, when Charlie made me watch the first one when we were in middle school, I basically became a super nerd overnight.”

“You did?”

“Well, I mean, about Star Wars. I could probably write you a ten-page paper about how Han shot first.”

“You don’t seem like someone who would be obsessed with Star Wars,” Cas said thoughtfully.

“Well thanks, man,” Dean said suppressing a laugh as shot a quick wink at Cas over his shoulder, “I try.”

Cas smiled that tiny half-smile of his, and they lapsed back into silence.

“We could… watch the next one sometime,” Dean said, and he wasn’t sure if he was just trying to fill the air, or if he actually wanted to see the look on Cas’s face at the end of _Rogue One,_ or if Cas was just starting to grow on him the way all of Sam’s friends eventually had, “or even knock out a couple of them if you’ve got the time... ”

“I would like that. What about Thursday night?” Cas was looking at him again, all expectantly, Dean could feel it without checking the mirror.

“Oh, uh,” Dean said nervously scratching the back of his neck, “that’d work for me, but Sammy works on Thursdays.”

Cas paused, thoughtful for a moment, “Well, Sam’s already seen it right?”

“I mean yeah, but do you really hang out just the two of us. It might be… weird.”

“I don’t see why not. I like you, Dean.” And Cas said it just like he said everything else. Like it was a fact. Like he had nothing in the world to hide. And Dean wasn’t sure why he found that so unsettling.

The thing was Dean preferred to dance around emotions.

Sure, he’d die for Charlie, and he’d probably get into a fistfight for Kevin, and he didn’t think there was _anything_ he wouldn’t do for Sam, but he didn’t exactly go around saying it. He just wasn’t one for chick flick moments. In fact, he tried to act like he didn’t like any of them at all most days. But Cas had a form of radical honesty that managed to make everything just a little weirder than it needed to be. So sure, Cas liked Dean as a person, but goddamn it, in his experience, liking someone; being a friend, being a brother; wasn’t a light topic. Dean wasn’t even sure if _he_ liked Dean, so he had no idea how Cas could say it like it was the easiest thing in the world when he barely knew him at all.

Maybe it was because he barely knew him at all.

Dean didn’t know. It didn’t matter.

“...Right. So,” Dean said as he pulled up to the curb in front of Gabriel’s house, “Thursday then?” and he willed Cas to ignore the yawning silence that had stretched between them since Cas had last spoken.

“Thursday.”

***

There was a black truck in the garage when Dean got home from work on Monday night. The garage door had risen slowly, and Dean had seen the light reflecting off of the bumper, and he had cursed and checked his phone for a text from John. There wasn’t one, but that wasn’t a big surprise. His dad had never been all that good about communication.

It did annoy him that he hadn’t gotten a text from Sam though. He had to be home from school by now and, really, how much work was it to shoot your brother a quick _Hey, Dad’s home. Mentally prepare for that,_ text.

But it was fine. Really it was. John had been due to come home any second. Sure he left without warning all of the time, but he usually wasn’t gone for more than a week. And Dean had missed him. He always did when his dad was out of town, but the routine of his life always shifted around John, and he wished that he’d had some sort of warning.

Dean closed the garage door and parked in the driveway instead.

As he approached the front door he found himself looking for other physical signs of his father: Dirt tracked in over the threshold, his father's old hiking boots discarded in the living room. His old hunting jacket hanging from one of their wall hooks. But there was nothing.

“ _Sam!_ ” Dean hissed as he caught sight of Sam doing his homework on the couch, “Dude why didn’t you tell me dad was home?”

Sam looked up at him and blinked in surprise, “He is?”

“His truck’s in the garage.”

“Shit.”

“I know.”

“Well I haven’t seen him yet, maybe he’s out on a walk or something?”

“Maybe,” Dean said, but he was already heading cautiously down the hall to investigate. When he reached the door to his father’s bedroom he paused for a moment and then knocked hesitantly.

“... Dad?”

There was no response.

Dean steeled himself and opened it a crack. And there was his dad, passed out on his bed. He was sprawled out on his stomach on top of the covers and still wearing shoes. Dean wasn’t sure if he was drunk or just that exhausted, but either way, it wasn’t a good look. Dean wished that he could say he was surprised. 

Dean trudged back to the living room to tell Sam. “Yep. He’s back alright. Sleeping.”

“Great,” Sam said.

Dean knew that Sam’s relationship with their dad was more complicated than his. Or maybe less complicated. There were parts of John Winchester that Dean hated with everything in his being. But he was their _dad_. Their blood. And that would always come first for Dean. But Sam, as he’d gotten older, had lost patience with John. John being home meant that Sam had to act slightly different. Dean did too, but that was par for the course. The reality of living with John. Dean had at least accepted it.

Then there was the matter of Sam's friends. Outside of Charlie, Sam hadn’t really introduced anyone in his current friend group to John, and even Charlie preferred to avoid him. Sam was smart enough to know that putting John Winchester in a room with openly gay Charlie, openly queer Gabriel, openly bi Chuck was a bad idea. Kevin and Cas were straight as far as Dean knew, but Kevin was Chinese, and Cas was… well Cas. The guy was just weird as hell.

“You probably shouldn’t have your D&D night here on Friday-”

“Yeah, I know, I’ll text everyone to let them know.” 

***  
John had spent the next morning walking around the house, groggy and, hungover, and upset that there wasn’t any beer in the house. As if Dean was old enough to buy any anyway.

Dean hadn’t been surprised that John hadn’t shown up at the shop all morning, and in some ways, he was even relieved.

When John wasn’t there Dean was the boss by default, but it had taken him a long time to work his way up to that level of respect with the guys, and whenever John came home things were a little less cut and dry. Most of the time John was too out of the loop to properly assign people jobs and keep everything organized. But none of the guys felt comfortable looking to Dean, a teenager, for instruction when his dad, the man who had hired all of them, was standing right there.

“Dad’s home,” Dean had told Bobby as they filled out paperwork in the back office during their lunch break. Bobby had cut back to part-time at the shop as of late because of his bad back, but Dean missed him on his off days.

“You doing alright?” Bobby asked.

“I’m fine Bobby,” Dean said, shooting him a reassuring smile, “I just thought that you’d want to know.” And Bobby had clapped him supportively on the shoulder because he knew when not to push.

***

When work had wrapped up for the day, Dean had driven home, pulled into the driveway, parked, sat in his car for ten minutes, and then changed his mind and driven to the Roadhouse.

Bugging Jo during her shifts had been a classic avoiding home pastime for Dean since he was sixteen, and the rundown bar always seemed to make him feel better.

The place was never packed, but it was pretty busy for a Tuesday night, and Dean was relieved to see an open stool at the bar.

“Joanna Beth, how are you doing this lovely evening?” he asked her, leaning his elbows onto the perpetually sticky surface of the bar.

“Was doin’ a lot better before you walked in,” She said, and Dean grinned one of his best grins at her until she rolled her eyes at him.

“Grab me a beer?” He asked innocently.

“You trying to get me fined for serving a minor Winchester? I don’t think so.”

“Oh come on Jo,” He said, and this too was a part of the routine.

He begged for a free beer. Jo said no. Then Ellen, Jo’s mom, came by to chat with him and offer him a free piece of pie. He always took her up on the pie but paid for it anyway because he’d feel guilty if he didn’t. Then At ten o’clock, when Jo’s shift ended, she’d sneak them each a shitty can of light beer, and they’d sit out on the back alley stoop and talk for a while.

These were the types of nights that kept his world turning, a kind of consistency that never got boring or oppressive. It was like a window into the kind of life that he was supposed to have, full of people with behavior he could predict, people who’d known him since he was just a kid but who loved him unconditionally anyway. These nights made him feel like a character in a sit-com, someone with a found family to come home to.

When the night reached its predictable end, Jo tossed him a White Claw over the counter and he didn’t even have the willpower to argue with her about it, and they went to sit out back.

They sat next to each other, Jo’s head tilted onto his shoulder, and Dean wondered if John would be awake to yell at him for staying out so late without calling when he got home. Like John had any room to talk.

“So, your dad’s home?” Jo asked, and Dean blinked at her, startled.

“How'd ya figure that?”

“I just guessed,” She said, and took a sip of her drink, “when Sam said we’d have to have the campaign at someone else's house.”

“Well, yeah. He’s back.”

“Are you okay?”

“First Bobby, now you," Dean laughed, "Why is everybody asking me that.”

“Maybe because you look like shit Winchester."

“Well, that's physically impossible Sweetheart,” Dean said, and he called up that smile. That smile that said, "I'm pretty, and I'm not tired, you're crazy for ever thinking otherwise."

She batted at his shoulder, “I just mean, John can be a hard person to live with, and if you’re having a hard time—”

“Jo. Can we not talk about it?”

And Jo looked at him, just a little bit of hurt flashing across her face as she leaned away from him back against the wall of the building. “Yeah. Okay.”

Silence fell between them.

“Jo?” Dean said after a moment.

“Yeah?”

“Have you— have you heard from Benny lately.”

Jo stared out at the dumpsters at the end of the alley, careful not to look at him as she spoke. “Yeah. Yeah, we talk sometimes. Seems like he’s doing good, he likes school so far. I think he really missed New Orleans.”

“That’s— that’s good. I’m glad he’s doing good.”

Another silence.

“Dean?”

“Yeah?”

“Why don’t you and Benny talk anymore?”

And Dean almost laughed. _Why didn't he and Benny talk anymore?_ It shouldn't have been funny at all, “We still talk.”

“Really? Because he asks about you too. When’s the last time you guys spoke to each other?”

Dean hesitated, “August I think?" and then, "He asks about me?"

“So not since he moved then.”

“Fuck off Jo.”

He couldn’t explain where things had gone wrong with him and Benny. They’d been so close throughout their last two years of high school, practically brothers. But then Benny had gotten into a school in New Orleans where he’d grown up, and he'd enrolled without a second thought.

Benny had suggested to Dean that he apply too. That they move down there together. Like Dean could afford out-of-state tuition. Like he was smart enough to get in. 

Like he could ever leave Sam.

Dean had helped Benny pack all of his shit before he'd flown down to move into the dorms. And Dean had asked him before he left, why in the hell he wanted to go so far away.

Benny had said something about Kansas having nothing for him, and it had felt like a lid closing on whatever the hell had been between them. Years of relying on each other first through everything: Through John's drinking, and Benny's parent's divorce. Through shitty breakups and bad birthdays. All of it wiped out, all at once. And Dean hadn't spoken to him since.

Because what the hell did you say to someone who doesn't think that you're reason enough to stick around.

**Notes for the Chapter:**

> Ha, you probably thought you’d seen the last of me. I mean, I’m kidding, but I am over a full week late with this update, so if anyone was waiting on this, I hope you haven’t already given up on this fic.
> 
> Anyway, I got distracted by college and binge watching WandaVision. This chapter is _suuuuper_ long though, so thank you for bearing with me. It might be another two weeks before I can put out the next chapter, I’ve got a midterm and a paper coming up :)


End file.
